Skip to main content

Full text of "Practical Organic Chemistry"

See other formats


246               PRACTICAL ORGANIC CHEMISTRY

action of bromine and caustic potash, phthalaminic acid is first
formed, which then yields the ammo-acid,
/COX                                   /CONHj,
C6H4<        >NII + HoO = CBH4<
NrCK                 ~                  XX)OH
xCONHo                              /CONHBr
C6H /            " + Bro      = C6H4<                  + HBr.
XCOOH                              XCOOH
xCONHBr                             ..NCO
QIV                        = CflH/          + IIBr.
XCOOII                                XCOOH
/NCO                                  /NHo
C6H4<;             + HoO      = CJI4<        "      +• CO.,.
XCOOII        "                      \COOH
The primary amines may also be obtained by the following
reactions :
1.  Action   of   alcoholic  ammonia  on   the alkyl iodides   jincl
nitrates,
C2HSI + NIT8 = C2H5NH2 + HI.    (Hofmann.)
Secondary and tertiary amines are also formed (see p. 156),
C2HSONO2 + NH3 = CoH5NIIo + IINO«.    (Wallach.)
2.  Reduction of the following classes of compounds :
nitro-compounds
cyanides
oximes
phenylhydrazones
C2H5NO2 + sH2 = C2H,NH2 + aH2O.    (V. Meyer.)
C2HaCN  + 2lI3 = CoH.CHoNIio.    (Mendius.)
CH3.CH:NOH + 2H2 = CH3.CH2.N.ri2 + H2O.   (Goldschmidt.)
CH8.CH:N.NHCGH5 + 2H3 = CH3.CH2.NH2 -f CflII5.NIIo.    (Tafel.)
3.   Hydrolysis of the isocyanides with cone. HC1, which occurs
in two steps :
C2H5NC + HoO = C2HBNII.COH
C2H5NH.COH + HoO = C2H5NH2 + HCO.OIT.
Th- three classes of aliphatic amines (primary, secondary, and
tertiary) may be disting'uished by their behaviour with nitrous